


Pretty in Pink Satin

by tryslora



Category: Teen Wolf (TV)
Genre: Community: kink_bingo, Crossdressing, Crossdressing Kink, First Kiss, Lipstick & Lip Gloss, M/M, Makeup, Pining, Stockings
Language: English
Status: Completed
Published: 2013-07-26
Updated: 2013-07-26
Packaged: 2017-12-21 10:39:26
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/899338
Author URL: https://archiveofourown.org/users/tryslora/pseuds/tryslora
Summary: <blockquote class="userstuff">
              <p>Stiles promised to get onstage in drag for the college GSA charity cabaret, but now that the night has come, he's not so sure. But his roommate is more than willing to help make sure he gets there.</p>
            </blockquote>





	Pretty in Pink Satin

**Author's Note:**

> This was written for the crossdressing square on my first kink bingo card for 2013. I just can't resist writing these two in dresses and being adorable. They are such pretty boys. Many thanks to my alpha M and my beta M for their quick turn-around times.
> 
> As always, I do not own the world or characters of Teen Wolf; I just like to play with them.

Stiles looks at the clothes spread out over his bed and takes a step back. “Maybe not.”

“You promised.”

Stiles wonders when Isaac learned the puppy dog look from Scott. Probably any time over the last two years, while Isaac lived in Scott’s home and nursed an unrequited crush. The fact that Isaac Lahey has the face of an angel and wide eyes framed with long lashes doesn’t hurt, and right now that gaze is turned on him and it is rapidly (oh so very rapidly) turning Stiles’s mind to mush.

He doesn’t have time for this. Not the clothes—no, those he has set aside time for. But this crush. That’s what he can’t handle right now. This sinking feeling that he is very much falling in love with his best friend’s best friend, who is still pining after Scott. Stiles has a long history of bad taste in crushes (Lydia, Danny, Derek), but this… this might be the most complicated yet.

The thing is… since it is Isaac asking, Stiles knows he’ll give in and do it.

“It’s not going to say anything about your sexuality,” Isaac points out. “Everyone in the GSA is doing it, gay or straight. The idea is that we’ve got the cabaret, we’ll have fun, the audience will have fun, and all the money we bring in will go to the shelter. It’s for charity, Stiles.”

Because charity is the thing that’s going to win him over.

No, really, it’s those eyes.

Stiles sighs. “Fine. But I’ve never done this before, and if I fall flat on my ass on stage in front of half the campus, I’m going to expect you to soothe my bruised feelings later.”

“I’ve got JD and Coke waiting for the after-party,” Isaac agrees. “Let’s get you dressed.” He lifts up the bra and panties, the lace falling limply over Isaac’s elegant fingers. “…Which requires you to take your clothes off, Stiles. It’s not like I haven’t seen you naked before.”

Stiles grabs the fragile underwear, and turns his back to Isaac. “That was in the lockers, when we were sweaty from lacrosse or cross country, and _everyone_ is naked. Or when we’re half awake getting dressed in the morning and it’s important to be quick so we don’t freeze our nuts off. It has _never_ involved lacy pink undies.”

“Well, now it will.” It sounds like Isaac is holding back a laugh, and Stiles doesn’t turn to find out if he is.

Instead, he strips his jeans off and shoves his boxer briefs after them, momentarily hopping awkwardly to kick them away and trying not to think about Isaac staring at his ass. When he pulls up the undies, there’s a problem. “Um. Where’s the rest?”

“That’s all there is.” Isaac puts his hands on Stiles’s shoulders turn him around. He’s definitely biting his lip, trying to hold the laugh in as he looks down at the panties and what they don’t actually cover up. “You just need to…” he motions with his hand at Stiles’s crotch. “You need to tuck. Sort of put yourself back between your legs, to smooth things out. It’ll help you fit.”

Isaac is making hand motions that involve the idea of touching Stiles’s dick. That dick is _never_ going to tuck neatly _anywhere_ at this point, but Stiles looks everywhere but Isaac and tries to do it anyway. His skin feels hot, and his cheeks are probably bright red, as he shifts and moves and tries to somehow get his dick between his legs and around his balls and oh holy crap. “This is slippery,” he mutters. “I have never worn silk boxers, and I am not sure I ever should. I don’t know if I like this. It’s itchy and silky and how the _fuck_ does a dude stay _tucked_ anyway?”

If Isaac’s puppy eyes are deadly, his smirk is even worse. It turns up at the corner, a slow light going into his eyes. “Problem, Stiles?”

His cheeks heat even more. “I’m a dude, and you just made me touch my dick. Of course there’s a ‘problem’.” Stiles licks his lips and grabs the bra—anything for a distraction. “Help me get this thing on.”

It would be one thing if Stiles had any experience with bras in general, but he’s never taken one off a girl, let alone tried to put one on anyone. It looks simple, but as soon as he tries to figure out how to get it on his own body, it becomes a tangled mess.

“Stiles.” Isaac’s hand falls on his shoulder, and Stiles goes completely still. “Here, let me help.”

Isaac holds it, and helps Stiles get his arms through without the straps twisting, the cups lying limp and flat against his chest. Isaac’s fingers brush along Stiles’s spine as he fixes the clasp at the back. He stands behind Stiles once it’s done. “See the baggies?” 

They lie there on the bed, filled with something that might be pudding, or hair gel, or some other soft, squishable liquid. Stiles isn’t sure he wants to know what it is, but when he picks one up, it has the heft and feel that he imagines a real breast might.

Not that he’s gotten his hands on one of those yet.

Isaac guides Stiles’s hand, helping him tuck the baggie into one bra cup, fluffing and primping until he has a single, solitary boob-like thing that seems kind of soft and realistic when he cups it. Stiles manages to get the second one in on his own, and glances in the mirror that hangs on the back of their door.

“I look silly with pudding on my chest,” Stiles points out.

“Well, soon enough you won’t. Turn toward me. I don’t want you looking until we’re done.” Isaac grips his shoulders and twists Stiles around until they are looking at each other.

He lifts the dress and raises it over Stiles’s head, waiting until Stiles raises his arms. Isaac helps guide the dress down, skimming along Stiles’s sides with a light touch, deft fingers smoothing over wrinkles as they find them.

It tickles.

It’s also making the tucking thing nearly _impossible_.

Stiles shifts his stance, trying to move things back where they belong without touching them. Or at least find a comfortable way to stand.

The dress isn’t something he would’ve picked out. For one, it has no sleeves, and a neckline that goes lower than he really thinks it should. But somehow Isaac fluffs and tucks and pokes and prods and the dress turns out to not show anything it shouldn’t. Stiles has a feeling magic is involved, even though he knows better.

“Sit.” Isaac pushes against Stiles chest, backing him up until the bed is in the way and Stiles has to sit, whether he wants to or not. Isaac sits next to him, a case of makeup open on the bed, and Isaac rifles through it, picking out sticks and tubes and little pots.

It’s all a mystery to Stiles.

“You have perfect eyes already, so we want to accentuate them. Look up.”

Stiles does, and Isaac touches something to his lower lid, dragging it carefully along. He does both eyes, then brings out a little brush-like wand to lightly touch it to his lower lashes. Stiles fights not to blink until Isaac’s hand moves away.

“Is that it?”

Isaac laughs. “We’ve barely started.”

Stiles wants to fidget, but Isaac has something that looks like an army of brushes and is touching Stiles’s face until his eyes drift closed. He wrings his hands together, trying to hold himself down beneath an onslaught of featherlight touches.

Having his eyes closed makes it so much more intense. He can’t see; he can only anticipate when the next gentle touch will fall.

A light brush across his eyelids, stroking lines in, shifting direction, outlining and enhancing. A harder line on the edge of his eyelid, and something tugging at his lashes.

“Just leave them closed,” Isaac murmurs, his hand beneath Stiles’s chin as he moves his face this way and that. “You’re more relaxed with your eyes closed. And don’t worry, I’m not going to hurt you. It’ll all wash off when you’re ready to let your glamorous side slip back into the closet.”

“I’m not in the closet,” Stiles protests, falling silent when a finger touches his lips. “I’m not,” he mutters.

“Mm.” Something brushes along Stiles’s cheekbone, followed by a drift of a touch, smoothing and stroking something into his skin. “So where are you on the Kinsey scale? Dead center?” Isaac’s thumb brushes over his lower lip. “I’m not blind. I know you’re not straight. You used to have a thing for Danny, right around the same time you had a thing for Lydia.”

“I had a thing for unattainable gods and goddesses,” Stiles manages to say without moving his mouth too much. When Isaac doesn’t say anything, he gives up and answers the question. “Slightly off-center, leaning more towards guys than girls. At least, if I count the number of crushes I’ve had, there’ve been more guys. I’m lacking in good physical evidence either way.”

He can hear the smirk in Isaac’s voice. “Well, I’d say silk panties are a winner, no matter who you’re with.”

“I’m a guy. Touch my dick, and it’s a winner.” Stiles goes quiet when Isaac tilts his head back, and his mouth falls slightly open. “What now?” he whispers, because his voice seems to have disappeared with Isaac holding him like this.

“Lips,” Isaac replies.

He starts with a pencil, drawing a careful outline around Stiles’s mouth. Stiles can imagine the way the lips are shaped, and when Isaac starts to carefully fill it in, he imagines the path that the brush takes. It’s easier to think of that, to live in his mind, than it is to pay attention to the careful touches that tug against his lip, pulling slightly before the brush drags onward, stroking sticky gloss over his skin.

It feels good.

It feels _really_ good.

Stiles makes a noise low in his throat, an involuntary squeak that trails off, wistful, when Isaac pulls back. “Are we done?” His voice is rough, a little shaky, and Stiles has to twist his hands into the sheets to hold onto _something_ and try to keep control.

“Almost.” Isaac ducks his head, not meeting Stiles’s eyes. “We just have to get your stockings on, and your shoes, and do something with your hair, then I’ll get dressed quickly and we’ll be ready to go.”

Stiles reaches for the stockings, but Isaac bats his hands away as he picks them up. Isaac crouches on the floor in front of Stiles, carefully angling the first stocking over Stiles’s toe. He unrolls it slowly, his hand stroking up over Stiles’s calf, smoothing the satiny soft fabric.

It’s torture.

“Isaac…” Stiles means to say that he can do it himself, because surely he can figure out how to get a thigh high stocking up to his thigh. But then Isaac looks up, his eyes doe-wide and his mouth slightly open, and every word in his mind flees. “Fuck…”

Isaac blinks and breaks the spell. “You have good legs for this,” he murmurs.

Stiles tries to agree, but all that comes out is a squeak. He shifts when Isaac’s hands reach his knee, moving again to let him nudge the stocking all the way up to the top of his thigh, where it sits, just tight enough to hold but not so tight that it’ll be uncomfortable.

Tucking? A thing of the past. An absolute impossibility.

Stiles is pretty sure that Isaac has a perfect view of his dick right now, peeking out from around the panties. His skin is flushed rose, and his heart hammers, fingers clenching when Isaac just barely grazes his fingers against Stiles’s rigid dick.

Stiles closes his eyes and whispers, “I’m sorry.”

“Don’t be.” Isaac pulls back enough to capture Stiles’s other foot. Isaac’s hand slides along the bottom of it, fingers warm and careful as he tugs the toe of the stocking over his foot. This time is even slower, fingers trailing over the strength of his calf, the crook of his knee. Isaac’s fingers circle Stiles’s thigh and by the time Isaac has the skirt nudged up enough to place the band around Stiles’s thigh, he is shivering.

“Don’t,” Isaac murmurs. “Am I scaring you?”

Stiles opens his eyes and shakes his head quickly. “Fuck. No. I mean. No. It’s just…” He grabs the hem of the skirt, trying to push it down, to hide his absolutely untimely erection. 

“Just _what_ , Stiles?”

“Do you know how hard it is to be your roommate sometimes?” Stiles blurts out. “I mean, I thought it would be for the best. Me and Scott… we’re a recipe for disaster as roommates. Constant video games, no studying, getting tossed out of college… pissing off our parents. So me and you, that’s good. Because then you’re not mooning over Scott, and I’m not being distracted, and hey, it works out _great_ most of the time.”

Now that he’s wound up, he can’t manage to wind down. “But then there’s _you_. And I hadn’t really spent _time_ with you before this, and you’re just another god in a long line of gods that are so far out of my league it isn’t even funny. Besides, Scott comes over and the two of you turn into a puppy pile and I can see it in your eyes, in the way you look at him. If I were a wolf, I bet I could smell it on you. You’re just… you’re _you_. And I want to pet you and make that kicked puppy look go away, and we won’t even go into the x-rated dreams, because honestly, none of that really matters when you’re falling in love with someone. That’s just sex, and sex is great, sure, I mean, I’d love if I could get some because the expiration date on my virginity is _so far past_ it isn’t even funny any more. But still. You’re _you_.”

Isaac blinks those huge eyes and Stiles realizes just how much he’s said.

“Fuck.” Stiles breathes the word out, wishing he could put some of those words back.

“Wow.”

“Sorry.” Stiles twists so he isn’t looking at Isaac. He manages to pull his legs up, tangled in the skirt, and tuck them under him on the bed as he puts his back to Isaac. “Maybe you should go without me tonight, because I’m pretty sure I couldn’t have fucked things up better than this.”

He can hear Isaac moving around, the shuffle of feet against the floor, the rustle of fabric as he quickly strips and dresses. He waits, because he doesn’t want to break the silence by saying the wrong thing, so instead he twists his hands in his laps and tries not to think about how the dress is wrinkling and he’s chewing his lipstick off.

“Stiles?”

“Hm?” He doesn’t make the mistake of turning to look at him.

“Do you still have a thing for Lydia?”

That’s not the question Stiles was expecting. He shakes his head. “Nope.”

“Danny? Derek?” 

Stiles shakes his head to both names, cheeks bright at the idea that the pack figured out about his crush on Derek. “That’s all long past.”

The bed sinks as Isaac sits next to him. Fingers thread through Stiles’s hair, tugging a strand out, twisting something hot through it and holding it carefully. “Then what makes you think I’m still pining after Scott?” Isaac murmurs, mouth too close to Stiles’s ear.

Stiles doesn’t have an answer to that, and thankfully Isaac doesn’t seem to need an answer, letting Stiles sit and think while he twists curls into Stiles’s hair. Fingers fluff through the warm strands when Isaac is done, and Isaac repaints the lipstick carefully.

“Done.” Isaac stands back and offers Stiles a hand. He takes it, finally taking a good look at Isaac, who has a slit in his skirt to show off his long legs. Stiles swallows hard because there is something incredibly hot about the way he has given himself tiny, spare breasts, and his curls seems just a bit longer, the makeup around his eyes turning them into something smoking hot.

Stiles stands slowly, turning with Isaac. In his heels, with Isaac still in bare feet, they are almost the same height. Isaac keeps his hand on Stiles’s hip, Stiles standing slightly in front of Isaac before the mirror. The girl who stares back at him has Stiles’s quick smile, the flush on his cheeks and chest, and the same honey brown eyes. But Isaac has definitely worked his magic with a makeup brush otherwise.

Isaac’s hands on his shoulders turn him, a hand under his chin tilting his face up just enough for Isaac to brush his lips lightly against Stiles’s mouth.

“I’m not pining for Scott,” Isaac says quietly. “I’m hoping maybe I’m not pining at all anymore.”

Stiles lets his hands find Isaac’s hips, fingers tangling in the soft skirt. There’s a temptation to push this, to see where it leads _right now_. It takes almost more control than he has to wrestle himself back from that edge. He smiles slowly, liking the way shadows fade from Isaac’s eyes when he does.

“Maybe we should discuss that after the cabaret,” he suggests.

“Maybe we should discuss it backstage.” Both eyebrows go up, and Isaac smirks.

“Do you want to spend the night redoing my lipstick?” Stiles counters. “It’s for _charity_ , Isaac. We can’t get distracted.”

“I don’t mind.” Isaac slides his thumb over Stiles’s bottom lip, smudging the color there, staining the pad of his thumb. “You look gorgeous like this, you know.”

“In a dress?” Stiles feels the flush coming again. “Is that it? You’re captivated by my girlish curves?”

“I could ask the same.” There is an uncertainty in Isaac’s tone, fear perhaps that this isn’t what he thought.

“I’m in it for all of you,” Stiles tries to keep it light, but the words come out serious. “I wasn’t joking. I mean… this… you…”

“I get it.” Isaac kisses the words away. “Let me get my shoes. We can finish this when we get back.”

Stiles shifts as soon as Isaac steps away, trying to retuck himself carefully back because bulges and skirts don’t match well at all. It’s not perfect, but it’ll do.

“Hey, Isaac?” Stiles waits until those wide, hopeful eyes turn to look at him before he smiles. “You can dress me any time. And undress me. Any time. Any way you like.”

A slow smirk starts, the corner of Isaac’s mouth turning up sharply. “I think we’ll keep the satin panties.”

The smile bursts into a grin. Stiles likes that idea.

He likes it a whole hell of a lot.


End file.
